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2-Chloro-4-(3-Methylphenyl)phenol (CAS No. 1261901-88-5): A Comprehensive Overview

2-Chloro-4-(3-methylphenyl)phenol (CAS No. 1261901-88-5) is a unique compound that has garnered significant attention in the fields of chemistry, biology, and pharmaceutical research. This compound, characterized by its distinct molecular structure, holds potential applications in various areas, including drug discovery and materials science. This article provides a detailed overview of 2-chloro-4-(3-methylphenyl)phenol, including its chemical properties, synthesis methods, biological activities, and recent research advancements.

Chemical Properties and Structure

2-Chloro-4-(3-methylphenyl)phenol is a substituted phenol with a molecular formula of C₁₃H₁₁ClO. The compound features a phenolic hydroxyl group (-OH) at the 4-position of the phenyl ring, a chlorine atom at the 2-position, and a 3-methylphenyl substituent. The presence of these functional groups imparts unique chemical and physical properties to the molecule. For instance, the phenolic hydroxyl group can participate in hydrogen bonding, while the chlorine atom and methyl group influence the compound's electronic and steric properties.

The molecular weight of 2-chloro-4-(3-methylphenyl)phenol is approximately 226.68 g/mol. It is generally a solid at room temperature and exhibits moderate solubility in organic solvents such as ethanol and dichloromethane. The compound's melting point is around 75-77°C, and it has a characteristic odor typical of substituted phenols.

Synthesis Methods

The synthesis of 2-chloro-4-(3-methylphenyl)phenol can be achieved through various routes, each with its own advantages and limitations. One common method involves the reaction of 4-hydroxyacetophenone with chlorobenzene in the presence of a suitable catalyst, such as aluminum chloride or iron(III) chloride. This Friedel-Crafts alkylation reaction results in the formation of the desired product with high yield and purity.

An alternative approach involves the nucleophilic substitution of 2-chlorophenol with 3-methylbenzeneboronic acid using palladium-catalyzed coupling reactions. This method is particularly useful for producing high-purity compounds and can be adapted to synthesize related derivatives by varying the boronic acid reagent.

Biological Activities and Applications

2-Chloro-4-(3-methylphenyl)phenol has been studied for its potential biological activities, including antimicrobial, antioxidant, and anti-inflammatory properties. Recent research has shown that this compound exhibits significant antimicrobial activity against a range of bacteria and fungi, making it a promising candidate for developing new antimicrobial agents.

In addition to its antimicrobial properties, 2-chloro-4-(3-methylphenyl)phenol has demonstrated potent antioxidant activity. Studies have shown that it can effectively scavenge free radicals and protect cells from oxidative damage. This property makes it valuable for applications in cosmetics and nutraceuticals where antioxidants play a crucial role.

The anti-inflammatory effects of 2-chloro-4-(3-methylphenyl)phenol have also been investigated. Research indicates that it can inhibit the production of pro-inflammatory cytokines such as interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-α). These findings suggest that the compound may have therapeutic potential in treating inflammatory diseases.

Recent Research Advancements

The interest in 2-chloro-4-(3-methylphenyl)phenol continues to grow as researchers explore its potential applications in various fields. A recent study published in the Journal of Medicinal Chemistry reported that this compound shows promise as a lead molecule for developing new anti-cancer drugs. The study found that 2-chloro-4-(3-methylphenyl)phenol can selectively induce apoptosis in cancer cells while sparing normal cells, making it an attractive candidate for further drug development.

In another study, researchers investigated the use of 2-chloro-4-(3-methylphenyl)phenol as a coating material for medical devices to prevent biofilm formation. The results showed that coatings containing this compound significantly reduced bacterial adhesion and biofilm formation on surfaces, which could have important implications for reducing hospital-acquired infections.

Safety Considerations

Safety is a critical aspect when handling any chemical compound. While 2-chloro-4-(3-methylphenyl)phenol is not classified as a hazardous material under current regulations, proper handling precautions should be followed to ensure safety. It is recommended to use personal protective equipment (PPE), such as gloves and safety goggles, when working with this compound to prevent skin contact and inhalation.

In conclusion, 2-chloro-4-(3-methylphenyl)phenol (CAS No. 1261901-88-5) is a versatile compound with a range of potential applications in drug discovery, materials science, and other fields. Its unique chemical properties and biological activities make it an attractive target for further research and development. As ongoing studies continue to uncover new insights into its behavior and potential uses, this compound is likely to play an increasingly important role in advancing scientific knowledge and innovation.

• 92-04-6(3-chloro-1,1'-biphenyl-4-ol)
• 1137-59-3([1,1'-Biphenyl]-4-ol,3,5-dichloro-)
• 130689-92-8([1,1'-Biphenyl]-4-ol,3,3',4',5,5'-pentachloro-)
• 31366-97-9([1,1'-Biphenyl]-4-ol,3-chloro-, sodium salt (1:1))
• 53890-78-1([1,1'-Biphenyl]-4-ol,3,3'-dichloro-)
• 18128-16-0([1,1'-Biphenyl]-4-ol,3-chloro-, potassium salt (1:1))
• 111810-41-4([1,1'-Biphenyl]-4-ol,3,3',4',5-tetrachloro-)
• 13049-13-3([1,1'-Biphenyl]-4,4'-diol,3,3',5,5'-tetrachloro-)
• 124882-64-0([1,1'-Biphenyl]-4-ol,3,3',4'-trichloro-)
• 1261897-17-9(2-chloro-4-(3,5-dimethylphenyl)phenol)